In Situ Generation and Intramolecular Schmidt Reaction of Keto Azides in a Microwave‐Assisted Flow Format

Painter, Thomas O.; Thornton, Paul D.; Orestano, Mario; Santini, Conrad; Organ, Michael G.; Aubé, Jeffrey

doi:10.1002/chem.201100768

Cited by 29 publications

(14 citation statements)

References 50 publications

(23 reference statements)

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“…Notably, keteniminium salts 6 44,45 and ethylene 46 have rarely been used in previous analogous transformations, and, to the best of our knowledge, no examples of their mutual [2+2] cycloaddition have been reported to date. We found that the keteniminium salts 6a and 6b (generated in situ from amides 7a and 7b) reacted with ethylene at 75 °C at atmospheric pressure to give the corresponding cycloadducts, which provided the target ketones 5a and 5b after hydrolysis (Scheme 4).…”

Section: Scheme 2 Strinc Sequencementioning

confidence: 99%

Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

et al. 2018

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An approach to 2-azabicyclo[n.2.0]alkane derivatives (n = 1, 2), which relies on a tandem Strecker reaction–intramolecular nucleophilic cyclization (STRINC) sequence of the corresponding 2-(ω-chloroalkyl)cyclobutanones (in turn prepared by [2+2] cycloaddition of keteniminium salts and ethylene) is described. The utility of the method is demonstrated by multigram syntheses of bicyclic proline analogues, monoprotected diamines, as well as parent 2-azabicyclo[4.2.0]octane.

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Section: Scheme 2 Strinc Sequencementioning

confidence: 99%

Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

et al. 2018

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“…[8] Almost all finechemical manufacturing is done in batch and the assembly of the exhaustive data necessary to make 'go, no-go' decisions about a chemical process is a waste-generating, resource-and labor-intensive exercise that frequently can take several weeks to many months to compile. [9] Flow chemistry can be performed on an infinitely smaller scale than batch making it safer by design [10][11][12][13][14] and larger amounts of material can be obtained by 'scaling out', which means running the process for a prolonged period of time and/or in parallel to produce only that which is required. [15] Novel developments in flow technology can add flexibility to the approach researchers take for the synthesis of important compounds.…”

Section: Introductionmentioning

confidence: 99%

Obtaining Kinetics From Continuous Processes: Sampling Multiple Time Points Concurrently With a Single Valve Rotation

et al. 2021

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The manufacturers of fine chemicals and pharmaceuticals are beginning to accept flow chemistry as a production alternative following the lead of commodity chemical manufacturers, who have been producing goods in continuous format for decades. The ability to trace time backwards by retracting the spatial length of a flow reactor is perhaps one of the biggest advantages of flowed synthesis. However, in the absence of an appropriate tool that would allow scientists to sample throughout the entire space of a production line, the theory is not possible to put into practice. A step in this direction has been taken with the invention of a unique, multi‐port valve/flow reactor that allows the chemist to simultaneously sample multiple timepoints of a chemical transformation with one single valve actuation, thereby capturing instantaneously the entire reaction course of the flowed chemical process.

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“…Aubéand co-workers integrated the intramolecular Schmidt reaction into a microwave flow-reactor. 22 Inspired by their pioneering work, our research showed that the ketone Schmidt reaction in MsOH−DME system can be performed quickly and safely with minimized amount of azide in a flow manner.…”

Section: ■ Introductionmentioning

confidence: 99%

Schmidt Reaction of Ketones in DME Solution in a Continuous-Flow Microreactor

Chen

Liu

et al. 2014

Org. Process Res. Dev.

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The Schmidt reaction, the treatment with hydroazoic acid in the presence of a strong acid, converts ketones to amides directly and has been broadly applied in organic synthesis. In this communication, the Schmidt reaction of ketones was carried out in DME solution in a continuous-flow microreactor and gave the amide products. The enclosed small-volume feature of the microreactor made this reaction safe, fast, and costeffective.

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In Situ Generation and Intramolecular Schmidt Reaction of Keto Azides in a Microwave‐Assisted Flow Format

Cited by 29 publications

References 50 publications

Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Obtaining Kinetics From Continuous Processes: Sampling Multiple Time Points Concurrently With a Single Valve Rotation

Schmidt Reaction of Ketones in DME Solution in a Continuous-Flow Microreactor

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